CZ298027B6 - Process for preparing epothilone-N-oxides and N-oxides of epothilones per se - Google Patents
Process for preparing epothilone-N-oxides and N-oxides of epothilones per se Download PDFInfo
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- CZ298027B6 CZ298027B6 CZ0286599A CZ286599A CZ298027B6 CZ 298027 B6 CZ298027 B6 CZ 298027B6 CZ 0286599 A CZ0286599 A CZ 0286599A CZ 286599 A CZ286599 A CZ 286599A CZ 298027 B6 CZ298027 B6 CZ 298027B6
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- epothilone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Silicon Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epoxy Compounds (AREA)
Abstract
Description
Způsob přípravy epothilon-N-oxidů a N-oxidy epothilonůProcess for the preparation of epothilone N-oxides and epothilone N-oxides
Oblast technikyTechnical field
Epothiolony A a B jsou známé; srovnej například DE 4 138 042, WO 93 10121 a WO 97 19086. Jmenovaný stav techniky je navrhuje jako terapeutické prostředky.Epothiolones A and B are known; cf., for example, DE 4,138,042, WO 93,10121 and WO 97,19086.
Dosavadní stav technikyBACKGROUND OF THE INVENTION
V PNAS USA 95 (1998) 1369 - 1374 jsou epothilony označovány jako užitečné terapeutické prostředky. V důsledku jejich terapeutických efektů se podle Angew. Chem. Int. Ed. 36 (1997) 2097 - 2103 bude dokonce opatřovat obsáhlá knihovna sloučenin tohoto druhu (extensive library of compounds).In PNAS USA 95 (1998) 1369 - 1374, epothilones are referred to as useful therapeutic agents. Due to their therapeutic effects, according to Angew. Chem. Int. Ed. 36 (1997) 2097-2103 will even provide an extensive library of compounds of this kind.
Podstata vynálezuSUMMARY OF THE INVENTION
Vynález se týká způsobu přípravy epothilon-N-oxidů, při němž se chráněný nebo nechráněný epothilon A nebo B o sobě známým způsobem převede na N-oxid.The present invention relates to a process for the preparation of epothilone N-oxides, wherein the protected or unprotected epothilone A or B is converted to the N-oxide in a manner known per se.
Tento postup podle vynálezu je s výhodou charakterizován tím že se N-oxidace provádí peroxykyselinou nebo dioxiranem.The process according to the invention is preferably characterized in that the N-oxidation is carried out with peroxyacid or dioxiran.
Předmětem vynálezu je rovněž epothilon-N-oxid (epothilon A-N-oxid) vzorceThe invention also provides an epothilone N-oxide (epothilone A-N-oxide) of the formula
r1, r2 = h, z = o; r = hr 1 , r 2 = h, z = o; r = h
Dále je předmětem vynálezu epothilon-N-oxid (epothilon B-N-oxid) vzorce:The present invention further provides an epothilone N-oxide (epothilone B-N-oxide) of the formula:
r1,r2 = h, z = o; r = ch3 r 1 , r 2 = h, z = o; r = ch 3
-1 CZ 298027 B6-1 CZ 298027 B6
Příklady provedení vynálezuDETAILED DESCRIPTION OF THE INVENTION
Příklad 1Example 1
Epothilon A-N-oxidEpothilone A-N-oxide
Ke 100 mg epothilonu A v 1 ml dichlormetanu bylo přidáno 100 mg 70% kyseliny w-chlorperoxybenzoové v 0,5 ml dichlorethanu. Po 6 hodinách míchání při teplotě místnosti bylo zředěno dichlormethanem a postupně vytřepáváno roztokem siřičitanu sodného a roztokem bikarbonátu sodného k odstranění přebytečné peroxykyseliny. Rozpouštědlo bylo odpařeno ve vakuu a zbytek byl rozdělen preparativní HPLC na sloupci Nucleosilu RP-18 (250 x 20 mm, mobilní fáze methanol/voda 60:40). Výtěžek 60 mg bezbarvého oleje.To 100 mg of epothilone A in 1 mL of dichloromethane was added 100 mg of 70% n-chloroperoxybenzoic acid in 0.5 mL of dichloroethane. After stirring at room temperature for 6 hours, it was diluted with dichloromethane and shaken successively with sodium sulfite solution and sodium bicarbonate solution to remove excess peroxyacid. The solvent was evaporated in vacuo and the residue was separated by preparative HPLC on a Nucleosil RP-18 column (250 x 20 mm, methanol / water 60:40 mobile phase). Yield: 60 mg colorless oil.
Rf= 0,60 (silikagel DC Alufolie, mobilní fáze dichlormethan/methanol 1:1);R f = 0.60 (silica DC Alufolie, mobile phase dichloromethane / methanol 1: 1);
ESI-MS (negativní ionty) m/z 510;ESI-MS (negative ions) m / z 510;
UV (methanol): Zmax = 240 nm;UV (methanol): λ max = 240 nm;
13C-NMR (CDC13): C-l 70,5, C-2 39,9, C-3 70,8, C^l 55,1, C-5 221,4, C-6 40,9, C-7 72,9, C8 37,6, C-9 31,8, C-10 22,8, C-l 1 28,0, C-12 58,0, C-13 55,8, C-14 32,2, C-15 75,5, C-16 144,5, C-17 111,4, C-18 143, 4, C-19 110,3, C-20 145,6, C-21 13,5, C-22 15,4, C-23 23,3, C24 12,0, C-25 16,5, C-27 18,2 ppm. 13 C-NMR (CDC1 3): C 70.5, C-2 39.9 C-3 70.8, C-L 55.1, C-5 221.4, C-6 40.9, C -7 72.9, C8 37.6, C-9 31.8, C-10 22.8, Cl-28.0, C-12 58.0, C-13 55.8, C-14 32, 2, C-15 75.5, C-16 144.5, C-17 111.4, C-18 143.4, C-19 110.3, C-20 145.6, C-21 13.5 C-22 15.4, C-23 23.3, C24 12.0, C-25 16.5, C-27 18.2 ppm.
Příklady syntézExamples of syntheses
Epothilon A-N-oxid: R1, R2 = H, Z = O', R = HEpothilone AN-oxide: R 1, R 2 = H, Z = O ', R = H
Epothilon B-N-oxid: R1, R2 = H, Z = O', R = CH3 Epothilone BN-oxide: R 1 , R 2 = H, Z = O ', R = CH 3
Claims (4)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19707505 | 1997-02-25 | ||
PCT/EP1998/001060 WO1998038192A1 (en) | 1997-02-25 | 1998-02-25 | Epothilones with a modified side chain |
Publications (2)
Publication Number | Publication Date |
---|---|
CZ286599A3 CZ286599A3 (en) | 2000-03-15 |
CZ298027B6 true CZ298027B6 (en) | 2007-05-30 |
Family
ID=7821415
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CZ0286599A CZ298027B6 (en) | 1997-02-25 | 1998-02-25 | Process for preparing epothilone-N-oxides and N-oxides of epothilones per se |
Country Status (25)
Country | Link |
---|---|
US (1) | US6359140B1 (en) |
EP (2) | EP1201666A3 (en) |
JP (1) | JP2001513098A (en) |
KR (1) | KR100494179B1 (en) |
CN (2) | CN1128803C (en) |
AR (1) | AR011878A1 (en) |
AT (1) | ATE221888T1 (en) |
AU (1) | AU736062B2 (en) |
BR (1) | BR9807742B1 (en) |
CA (1) | CA2281105A1 (en) |
CZ (1) | CZ298027B6 (en) |
DE (2) | DE59805110D1 (en) |
DK (1) | DK0975638T3 (en) |
ES (1) | ES2183338T3 (en) |
HK (1) | HK1023774A1 (en) |
HU (1) | HU228851B1 (en) |
IL (1) | IL131343A (en) |
NO (1) | NO327211B1 (en) |
NZ (1) | NZ337195A (en) |
PL (1) | PL190422B1 (en) |
PT (1) | PT975638E (en) |
RU (1) | RU2201932C2 (en) |
TW (1) | TW480263B (en) |
WO (1) | WO1998038192A1 (en) |
ZA (1) | ZA981575B (en) |
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Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59609305D1 (en) * | 1995-11-17 | 2002-07-11 | Biotechnolog Forschung Gmbh | Epothilone derivatives and their production |
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-
1998
- 1998-02-25 EP EP02001063A patent/EP1201666A3/en not_active Ceased
- 1998-02-25 DE DE59805110T patent/DE59805110D1/en not_active Expired - Lifetime
- 1998-02-25 BR BRPI9807742-2A patent/BR9807742B1/en not_active IP Right Cessation
- 1998-02-25 AT AT98912388T patent/ATE221888T1/en active
- 1998-02-25 DE DE19880193T patent/DE19880193D2/en not_active Expired - Lifetime
- 1998-02-25 CA CA002281105A patent/CA2281105A1/en not_active Abandoned
- 1998-02-25 HU HU0002189A patent/HU228851B1/en unknown
- 1998-02-25 KR KR10-1999-7007773A patent/KR100494179B1/en not_active IP Right Cessation
- 1998-02-25 PT PT98912388T patent/PT975638E/en unknown
- 1998-02-25 WO PCT/EP1998/001060 patent/WO1998038192A1/en active IP Right Grant
- 1998-02-25 JP JP53730098A patent/JP2001513098A/en not_active Withdrawn
- 1998-02-25 IL IL13134398A patent/IL131343A/en not_active IP Right Cessation
- 1998-02-25 CN CN98802842A patent/CN1128803C/en not_active Expired - Fee Related
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1999
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993010121A1 (en) * | 1991-11-19 | 1993-05-27 | GESELLSCHAFT FüR BIOTECHNOLOGISCHE FORSCHUNG MBH (GBF) | Epothilones, process for preparing the same and their use as medicaments and as plant protecting agents |
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PD00 | Pending as of 2000-06-30 in czech republic | ||
MK4A | Patent expired |
Effective date: 20180225 |